


Roll For Initiative

by Mewchan



Category: Dangan Ronpa: Trigger Happy Havoc, Mahou Shoujo Madoka Magika | Puella Magi Madoka Magica, Mystery Skulls Animated, Stranger Things (TV 2016), Thor (Movies), おそ松さん | Osomatsu-san (Anime)
Genre: Other, That's it, enjoy my insanity, just a fun self insert romp of dnd, literally the only reason for the rating is brief sex jokes and cursing, may have some ooc writing at times i'm not sure, nbd, that i had to write for therapy
Language: English
Status: Completed
Published: 2018-07-10
Updated: 2018-07-10
Packaged: 2019-06-08 08:07:17
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,128
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15239061
Author URL: https://archiveofourown.org/users/Mewchan/pseuds/Mewchan
Summary: “Will, I appreciate you bringing friends to make up for the fact Dustin and Lucas are out of town but...” Mike muttered to his non-binary friend who shared his best friend’s name, looking over the group that sat around the table, “Where do you even meet people like that?”In which the author has to write self-insert fanfic for their therapist about them and their favorite characters hanging out, and playing DND apparently. Shenanigans ensue. (I am sorry and yet not for this.)





	Roll For Initiative

**Author's Note:**

  * For [my therapist](https://archiveofourown.org/gifts?recipient=my+therapist).



> If you clicked on this, you are a brave soul and you win 10 pearl points. If you make it to the end (and maybe leave a comment/kudos) you'll be rewarded the best saxophone song in existence. I love you all.

“Will, I appreciate you bringing friends to make up for the fact Dustin and Lucas are out of town but...” Mike muttered to his non-binary friend who shared his best friend’s name, looking over the group that sat around the table, “Where do you even meet people like that?”  
  
Their main and usual group consisted of the usual three, Mike - the DM, Will - the cleric and best friend of the DM, and Will M - the enby who brought some strange characters to DND, along with their girlfriend Spring. Dustin and Lucas were out of town for a science fair that required duos and they were chosen from their class. Of course that’s not to discount the truly strange cast that Will M brought along.  
  
“I do say that this Dee and Dee situation would be much better if I could get a drink. Make it a party and all.” One guest piped up as he leaned back in his chair, fiddling with a twenty sided dice as his cape draped on the ground.  
  
“Yes I would also love a nice cold beer, would really cement the scene. Or a nice red wine perhaps, ey Buraza?” Another spoke with an obvious trying to sound American but really really failing to do so accent, as he adjusted his sunglasses (indoors no less) and nudged Will M.  
  
“Ah sorry, don’t think you’ll get any good, or really any cheap alcohol here. Mike’s guests aren’t really allowed to drink.” Will M explained sadly.  
  
“Plus Mrs Wheeler tends to keep the alcohol to herself. Sorry Loki, Kara, you’ll have to do without tonight.” Spring teased, resting her head on Will M’s shoulder.  
  
“A true pity. It would suit nicely with such a game.” The green cloaked guest, now known as Loki sighed a bit, though playing it up for the Drama Of It All™.  
  
“For a true battle of wits and courage, a warrior need not drink. Besides most of the guests here are under 21, and therefore it’s not legal for them to consume alcoholic beverages.” One of the larger guests responded, beefy arms crossed in front of her as she spoke.  
  
“Sakura-chan has a point, I mean I’m only 14.” The smallest girl of the party spoke up, leaning a bit on the table as her pink pigtails swayed a bit from her movement.  
  
“A practical infant.”  
  
“Listen.” The girl responded with a deadpan expression. “I didn’t sell my soul for humanity to break the whole magical girl curse thing to be called an infant from a trickster god that can’t beat the Jolly Green Giant in a boxing match.”  
  
“MADOKA THAT WAS ONE TIME.”  
  
“I mean I had my money on the Hulk.” The largest of the males in the group piped up, leaning his skull head on his rather large hand. A truly terrifying yet amazing ghostly specimen to say the least.  
  
“Can we PLEASE get to the game??” The truly exasperated DM Mike groaned. “I have a lot planned tonight!”  
  
“Fine fine. Does everyone understand the explanation I gave before we got here?” Will M quickly asked their guests.  
  
“I would suggest we do a roll call before we start cause I don’t know who any of you guys or your characters are.” Mike muttered, bringing out a piece of paper to write notes for himself.  
  
“Very well. Should we go around the table from our friend Will?” The buff white haired girl Sakura asked.  
  
“Sure. Whatever works.” Mike sighed, getting ready to write.  
  
Will M spoke up first. “Well you already know me and my Tabaxi character Jia. Spring isn’t playing again.”  
  
“Aw why not Spring?” The smaller boy Will asked with a pout.  
  
“I just wanna observe this chaos.” Spring grinned. “Next time I promise.”  
  
“Okay and next to you?”  
  
“My name is Karamatsu Matsuno, and my character is a tiefling bard named Aetros, he’s .. ah am I saying this right.. chaotic good?” The man in the glasses asked, now known as Karamatsu.  
  
“Yes you’re saying that right.” Will offered and Karamatsu nodded, with a big stupid grin.  
  
“Uh I’m Lewis Pepper, my character is a minotaur wizard named Podkurat Strongrunner. He’s lawful neutral.”  
  
“I’m Madoka Kaname! My character is an Aasimar archer named Sayaka! She’s lawful good and she just wants to help the princess!” Madoka grinned, “I even drew her see?” She showed her sketchbook and Mike actually managed to crack a smile.  
  
“She’s really good!” Will smiled and Madoka beamed excitedly, obviously already getting into this.  
  
“My name is Loki, but you probably already know that. My “character” is a high elf rogue named Fenrir. He’s chaotic neutral because Will M told me I couldn’t make him chaotic evil.”  
  
“Cause you’re not even chaotic evil, you’re chaotic neutral at best.” Will M reminded him and he huffed a bit, looking away indignantly.  
  
“My name is Sakura Oogami. My character is a half orc barbarian named Rahizura. She is neutral good and will probably protect the weaker members of the party.” Sakura nodded as Madoka beamed and waved at her.  
  
“That is so adorable.” Lewis smiled a bit, and Sakura gave a soft smile in return.  
  
“I’d tap that any day~” Karamatsu grinned and Sakura huffed, smile disappearing and a glare towards the flagrant man replacing it.  
  
“Okay okay whatever, let’s get this started!” Mike huffed, and began to set the scene. “In the Valley Kingdom of Alderia, the King and Queen are at their wits end! Their strong and proud princess Gu’rea has been kidnapped by a hoard of monsters. They offer a massively large reward to whomever can bring the princess home, but every adventurer who tries dies horribly. But you and your friends aim to bring them home. You start in the Valley Forge Pub, what do you do to begin?”  
  
The ghostly Lewis speaks up. “I look around the pub to see who might look like they have information.”  
  
“Thank you for taking this seriously Lewis. In the pub is a group of Tabaxi traders gambling, a couple of dwarf miners drinking, an old haggard wizard sitting at the corner table and the tall and intimidating elf bartender, along with your ragtag group. Who do you approach?”  
  
“I say the haggard wizard.” Will offers and the trickster god laughs.  
  
“You’re only saying that because your character is a wizard.” Will huffed indignantly as Madoka spoke up.  
  
“Well older characters may have more wisdom to impart, he’d be a good place to start!” Will grinned at her and Loki rolled his eyes at her.  
  
“I’m just saying the miners might be more fun to talk to. Or the traders.”  
  
“You’re just saying that cause they are drinking and gambling. It is your choice Lewis.” Sakura responds, throwing a glance at the hulking specter. He nods, as he holds his dice in his large hands.  
  
“Very well, I’m going to talk to the haggard wizard, see if he gives us any information.” Mike nods and continues his narration.  
  
“As you approach the wizard he puts a hand up before you can say a word.” Mike narrated, mimicking the motion in turn. “His voice is very deep and his words have an arcane tone to them. He speaks: Travelers I already know the path you wish to take and I must warn against it. Many who do what you wish to perish in gruesome and disturbing ways.”  
  
Karamatsu visibly winces. “Do we have to do the main quest?”  
  
“Yes.” The group intoned, very much at the same time.  
  
“Ok...”  
  
Mike resumes his speech as the haggard wizard. “Turn back while you still have the chance travelers. You still have a chance to survive-.”  
  
Madoka quickly interrupted. “The Princess is in danger! If everyone wusses out she’ll be stuck there forever!! We have to at least try!”  
  
“Well said Madoka.” Sakura nodded.  
  
“Is that you saying it or your character Sayaka saying it?” Mike asked, a little exasperated.  
  
“Uh make it Sayaka!”  
  
“Okay roll for persuasion.” Madoka bit her lip and rolled a twenty sided die. She perked up seeing the number on the pink die.  
  
“I got an 18!” Mike nodded, impressed and thought a second before he responded.  
  
“The haggard wizard gives your response some thought before he points a gnarled and wrinkly finger towards the bar.” Mike pointed as well as he spoke. “He responds wearily: At the bar, the bartender Yvonne has a map that will lead to the dungeon of the Monster of Old. He is the one who keeps the strong and proud princess and defeating him will allow you to free her from his monstrous-“  
  
“We GET IT. Can we move on now, or are you gonna posterize for a while longer?” Loki groaned, leaning back in his chair once more. Mike gave a scowl at the trickster god and picked up his dice as he continued.  
  
“So the wizard points the way and you all make your way to the bar where the bar intimidating elf bartender Yvonne is cleaning used mugs. Who shall speak?”  
  
“I roll to flirt with her.” Karamatsu excitedly pipes up, leaning over Will M as he grins widely.  
  
“You’re gonna- She hasn’t even said anything yet! Why now??” Mike stammered in annoyance.  
  
“Well maybe she’ll hand over the map quickly if I remind her of her beauty~~” Karamatsu grinned, posing as his sunglasses gleamed. He was very much the sunglasses emoji.

“Painful.” Spring teased as Mike rubbed his temples, muttering to himself something about at least Dustin didn’t flirt with every npc..  
  
“Fine what do you say to her?”  
  
Karamatsu snaps his fingers and poses before he responds. “I walk up to her and lean on the bar. Then I bring out a rose from my lapel and say ‘My dear, the stars have fallen out of the sky to be in your eyes. Perhaps I can procure the map to the monstrous beast and save the princess, then I can take you on the adventure of an existence~~’ then I wink!”  
  
Everyone at the table grimaced, including Lewis which was a feat considering his face was a skull. “Roll for.. charisma..?” Mike groans, rubbing his temples yet again.  
  
Karamatsu grins as he rolls his sparkling blue d20 then looks up after reading the number. “Is a 1 good? I have +3 charisma.” Loki wheezed audibly, trying so hard not to cackle.  
  
“You rolled a nat 1, your modifiers can’t save you now.” Spring teased and Karamatsu paled.  
  
Mike took this opportunity to fucking decimate Karamatsu’s dumbass of a character. “Just after you say this a large dragonborn woman walks through the doorway to see her WIFE THE BARTENDER scowling at you.”  
  
“OHHH HER WIFE!!!” Loki cackled and Karamatsu stammered for a response.  
  
“H-How was I to know she was married!!”  
  
“Only know do you notice the red stone ring on the elf woman’s left ring finger, and notice her wife’s matching ring on her own. Said wife is steaming, quite literally as smoke comes out of her reptilian nostrils.”  
  
“C-Can we stop posterizing?” Karamatsu whimpers in fear.  
  
“No no keep going this is too good!” Spring wheezes, and Will M is trying their damnedest not to laugh too.  
  
Mike grins, now obviously enjoying the power he holds in his grasp. “The scary dragonborn wife gives you a look that could curse you just from that and speaks in a deep gravelly voice. ‘Is this tiefling bothering you Yvonne? Shall I burn him to a crisp?’ Anyone wanna jump in to save Aetros?”  
  
Will M groaned breaking the silence that had happened after Mike offered to save Karamatsu’s character. “Ugh fine, I jump in and try to fix the mess he made. I push him out of the way and I say something like ‘Sorry about him, he’s a flirt and he doesn’t pay attention to his surroundings and I swear we don’t speak on his behalf.’”  
  
“Aww..” The others pouted.  
  
“Well alright roll for persuasion.” Mike shrugged and Will M rolled their dice, smiling a bit when it landed on a 17. “Alright that works. Yvonne then asks what exactly we want anyhow, if Aetros didn’t represent you.”  
  
“I say ‘Well we DO want the map to save the princess, but the flirting was all him.’ And bow a bit to show I’m good.” Will M quickly rolls and nods, seeing a 16 on the dice.  
  
Mike glances over before he responds. “She looks you over and nods. ‘Very well. This is the map that will lead you to the monster’s lair. Be careful with it.’”  
  
“Yes! It worked after all!” Karamatsu grinned.  
  
Mike smirked before he continued. “‘Oh and your tiefling friend is no longer allowed in my bar or he will be killed.’” Karamatsu could only whimper at that.  
  
“Awesome now let’s head out!” Madoka grinned.  
  
“So now, You guys have to see if you can read the map.” Mike grinned a bit.  
  
“Wait what, you mean we might not even be able to READ IT??” Loki growled angrily.  
  
“Relax, it’s just a matter of who rolls highest being the only one to read the map, Mike does this schtick like almost every time.” Spring laughs and Mike groans a bit, annoyed that Spring so easily saw through his ploy.  
  
“… Anyhow roll to see who can read the map.” Mike huffed and Spring grinned knowingly. Everyone rolled and a chorus of varying emotions swept over the party. “Okay now who’s got the highest number?”  
  
“… Does a 1 count?”  
  
“No Kara.”  
  
“I think Sakura got the highest number, she got a 20, plus 1 for arcane knowledge too.” Lewis offered and Sakura smiled softly. “Looks like we’re in your hands barbarian.”  
  
“Alright, now she’s someone I can trust!” Madoka beamed and Sakura blushed a slight bit at the praise.  
  
“Then I will proceed to read the map and guide my fellow travelers.” She affirmed. “We head for the monster’s lair.”  
  
“Okay so you all make it into the Enchanted Forest, but you can hear wisps of laughter in the trees. What do you do?”  
  
“I mean we should probably investigate what the wisps of laughter are, they could be dangerous-“  
  
“I ROLL TO SEDUCE THE WISPS” Karamatsu quickly interrupted Lewis who groaned at the interruption.  
  
“Absolutely not.” Mike immediately replies.  
  
“Please! I could try and get them to not attack us!”  
  
“….. What do you say to the wisps.” Mike is just. Done. At this point.  
  
“Wisps we mean you no harm, we simply wish to pass through your lovely forest, but if you cannot let us all go through you may take me as your own to have and to hold through many cold nights~~”  
  
“I legitimately threw up in my mouth a little.” Madoka admits, and Sakura looks a little green herself.  
  
“What do you roll.”  
  
“Uhh…” He rolls and winces. “A… 3?”  
  
“Are you prepared for the kind of death you’ve eared, little man?” Will asks as Mike rubs his hands together. Karamatsu winces.  
  
“Oh no.”  
  
“Goddamnit we’re doing this again.” Will M groans. “No no I quickly try to placate the wisps and tell them NOT to do anything to the blunt idiot, and that we’re just passing through.”  
  
“Roll to see if you can counter Kara’s roll?” Mike raised an eyebrow.  
  
“I got a 13.”  
  
“Good enough, the wisps mutter to themselves, spit upon Aetros and depart, dropping 5 gold a piece and a wand, so your party gains 20 gold and an unusual wand. Do you continue forward?”  
  
“May I investigate the wand before we continue?” Loki asks, fiddling with his dice. The others share a look then nod. “Then I pick up the wand and attempt to use a spell, see how well it works.”  
  
“What spell, where do you aim and roll for attack.” Mike rattles off.  
  
“I’ll try casting eldritch blast and aim at the tree next to Podkurat.” He responds before rolling his dice. “Curses I got a 7.” Will stiffened at the number and Madoka patted him on the back quickly.  
  
“The wand seems to short out when you attempt the spell and instead you get a nasty shock, take off 3 points of arcane damage.”  
  
“Oof.” Spring winces and Loki shakes his head, muttering to himself.  
  
“Then I’m content, let’s continue forward.”  
  
Time passed and soon the group was at a large cave entrance. Mike began to narrate once more. “The cave is guarded by a changeling, their hair long, white and wispy, and their eyes a piercing ice blue. Their gender is ambiguous and they give your group a quick look over.”  
  
“I ROLL TO-“  
  
**“NO”** Everyone immediately snaps at Karamatsu who quickly puts his hand down, with a curt ‘Never mind.’  
  
Mike rolls his eyes before he continues. “They begin to speak” he immediately takes on the role, eyes almost seeming to glaze over as he speaks, hand outstretched to give the illusion he is the character. “I am the Seer of Sight, the Giver of Punishment and the Learner of Truths. I offer a riddle before your party can advance. Can you solve the riddle I put forth?”  
  
“Ooh a riddle, now this I like~” Loki almost purred, leaning on their wrist interested.  
  
“My riddle is thus: What is something that fades and goes over time, but some of it’s residue will always remain?” Mike responds before suddenly breaking character when Karamatsu snorts.  
  
“Is.. Is it love makin-“  
  
“NO. Good god not everything is about … that. Gross.” He huffs then goes back into character. The rest  of the group continues to think it over.  
  
“Is it picture filament? Like for photographs?” Lewis offers and Mike shakes his head. “Oh wait that wouldn’t exist in the time frame would it?”  
  
“Don’t think so specter. Perhaps a monarchy?” Loki offers and Mike blinks a bit before shaking his head.  
  
“That was rather obscure. I think the answer is the glare of the sun after you look at it. With the sun spots you see after you blink.” Sakura offers and Mike again shakes his head.  
  
“No but that is a clever answer.”  
  
“Oh! I think I know!” Madoka beams. “Memories!” Mike immediately assumes the role again.  
  
“Very good Clever Sayaka, Wise Aasimar and Protector of the Group. You may all enter, but be warned, the dungeon seeks not to be a haven but to be a monstrous plight to all who enter. You will most likely perish.”  
  
“Then that’s a sacrifice we must be willing to make. Let’s go.” Lewis mutters.  
  
“Easy enough for you to say! You’re already dead!” Karamatsu whines and Lewis’s bright fiery hair (literally made of fire) flares up angrily at the quip from the sunglass wearing man who squeaks in fear.  
  
“Easy with the fire Lewis!! My mom will kill me if I burn the house down during DND!!” Mike yelps and Lewis quickly tones his flames down. “Anyhow you begin your quest into the dungeon.  
  
Simply due to the author’s inability to write fight scenes, we will skip over the minor thugs and such in the dungeon and cut to later. The party was very beat up and it could be said that neither of the Will’s had any healing spells left, just a handful of attack spells and one resurrect. And they were at the gate to the boss.  
  
“As you enter the dungeon, you can immediately smell the lingering stench of death, corpses in various states of decay litter the floors and the walls are dingy and musty with the stains of the adventurer’s past. Have you all made it into the room?”  
  
“Yes. We have.” Sakura intones. Mike snaps his fingers before he continues.  
  
“As soon as you all enter, the door to the dungeon immediately snaps closed. There is now no going back. And then you hear it.” Mike stands and starts stomping on the ground as he intones sound effects. “Boom, boom boom. Footsteps, but inhuman ones sound from the depths of the room. Boom boom boom, and a shriek, then a sound similar to the wind being sucked from the room. Out from the shadows emerges a large, pulsing monster. It is simultaneously nothing and everything all at once, long eldritch tentacles and black slime ooze and whip around, one of which holding the princess, who screams as loud as she can for help. Roll for initiative.”  
  
After the rolls were dealt, and turn after turn passed, it was in the final stretch of the battle, If a character was alive, they were on their last hit point. It seemed to be the end.  
  
**Seemed.**  
  
“Kara, it’s your turn, what do you do?” Madoka whimpered, nervously gripping her sleeve. He gently chuckled and fixed his glasses.  
  
“I have a plan, and it’s farfetched, so you guys have to trust me. Do you trust me?”  
  
“It is literally against my better judgement to trust you, but at this point its based on win or lose, life or death so yes fine I trust you.” Loki responds and the others also hesitantly nod. He chuckles and stands, pointing intensely forward at Mike.  
  
_**“I ROLL TO SEDUCE THE ELDRITCH MONSTER!!!!”**_  
  
_“YOU HAVE GOT TO BE FUCKING KIDDING ME.”_ Mike yelped, absolutely confused out of his mind and everyone else’s expressions ranged from ‘Is he serious’ to ‘Oh fuck not again’. “EVERY and I mean EVERY single interaction that you’ve attempted to flirt has lead you to rolling absolutely vile numbers and you expect this to work??!”  
  
“It’s all I have left, I’m out of spell slots.” Karamatsu admitted and Mike stared at him dumbfounded for a second. When he finally works up the motivation to continue he waves as if to ask what he’s gonna say and Karamatsu poses before launching into a speech. “Dear Eldritch God, if I may call you Eldie, I implore you to seek the goodness in your heart, as you are everything evil and everything good all at once by nature of being eldritch! Please see that I mean you no harm and I purely wish to belong to you in a loving, inky and all encompassing embrace and see that I can fit your needs far greater than any princess in any land can if only you will trust me! I too am nothing, but I am also willing to be your everything if you just accept me!”  
  
“Am I dreaming? Is this what dreaming feels like? Can Mami wake me up now??” Madoka whines, and Will gently pats her on the back.  
  
“What. Do. You. Roll.” Mike struggles to say and Karamatsu steels himself before rolling his sparkly blue dice.  
  
“Is a 20 good?” He asks and the group stares at him dumbfounded. “What? … Oh I also have plus 3 charisma-”  
  
“SO THE ELDRITCH GOD DROPS THE PRINCESS AND PICKS YOU UP.” Mike rambles, practically seeming to have gone off the deep end. “It cradles you in it’s all encompassing, inky grasp and speaks to you directly into your brain in dark arcane knowledge that you SOMEHOW are able to understand about you being so fucking romantic or some shit and it carries you off and you get married and have weird tiefling-slash-eldritch babies and you save the princess!!!!” Mike leans on the table for a second, then stands. “Excuse me for a minute.” He mutters then walks upstairs.  
  
“… I think that went well!”  
  
——  
  
“Mom I need you to do me a favor.” Mike quietly asked his Mom, who had been busy washing dishes but stopped when Mike got her attention so softly. “I need you to loudly say we’re done with DND and that we’ve been playing long enough and we need to stop.”  
  
“… Sweetheart you’ve only been playing 3 hours, that’s a record short time for you are you okay?” Karen Wheeler asked, absolutely confused.  
  
“Mom, Will M’s friends are freaking insane and I need a break, please for the love of Holly just do this one thing for me, I will do anything.”  
  
“….Including babysit Holly for a week?”  
  
“Yes so long as Will comes too, she really likes him.”  
  
“Fair enough.”  
  
——  
  
From downstairs, the others kept looking around. “Well now what do we-“  
  
“Michael you’ve been playing long enough, you should really send your friends home now!”  
  
“But MOM we’ve only been playing 3 hours!”  
  
“It’s a school night young man, and you’ve got a big test tomorrow, send them home!”  
  
“UGH FINE.” Mike came downstairs. “You guys gotta go.”  
  
“Same time next week?” Loki teasingly asked.  
  
“Absolutely not.”  
  
“Oh…”  
  
“You can come back Madoka, you and Sakura, and maybe Lewis but the rest of you need to never come back ever.”  
  
“Oh.” Karamatsu intoned.  
  
“Now please get out of my house.”  
  
“You know you love us~~” Spring teased.  
  
“Shush. For my sanity please.”  
  
“Yes your DM’liness.”

**Author's Note:**

> You made it! Congrats. Have the best saxophone song ever: Baker Street by Gerry Raferty. Your ears will thank me.


End file.
